Bill Gates' worst decisions as CEO, according to a longtime Microsoft exec

Bill Gates served as Microsoft CEO for nearly 25 years, until he stepped down in 2000.

In that span, he turned a two-man startup into a tech juggernaut worth hundreds of billions of dollars, becoming the world's richest man along the way.

But every great CEO makes mistakes, and according to Brad Silverberg, who's spent nine years as Microsoft's SVP from 1990, Gates made two critical mistakes that hampered the company's business in some ways: His weak lobbying efforts and failure to take advantage of the internet early on.

"Top of the list for me is that Bill did not engage - either himself or the company - in the political process early enough. When Microsoft's competitors were effectively lobbying the government, Bill's attitude was the government should just go away and leave Microsoft alone," Silverberg wrote in a Quora Q&A session held Friday.

Silverberg writes Gates didn't engage the government and politicians early on because he believed the company was competing fairly and creating enough value for the customers. But that approach was a "disaster," he writes, as it essentially made the US government and the EU to "declare war on Microsoft."

In 2000, Judge Thomas Penfield Jackson ruled that Microsoft broke antitrust law by unfairly bundling Internet Explorer with Windows. Although Microsoft eventually settled the case with the Department of Justice in 2001, many believe it hurt Microsoft's dominance in the field.

Silverberg also believes Gates dismissed the threat posed by the internet because he wanted to protect Microsoft's Windows empire at the time. He writes:

Bill also had a difficult time figuring out how to respond to the opportunity / threat of the Internet. It's understandable. When you own Windows in the late 90's, life is good and why would you want things to change? Bill's view was to protect Windows, and didn't come up with an approach that kept Windows and Microsoft's systems strategy at the forefront. The result is that Microsoft's strategic position declined in the 2000's. It's now coming to grips with the new reality and making necessary, if belated, changes.

But Silverberg still has a lot of respect for Gates and believes he's one of the greatest CEOs ever.

He writes in another Quora post that Gates had the early vision to build a software empire and a massive platform business, while making important strategic decisions that allowed Microsoft to own both the consumer and enterprise space, which is a rare feat for any tech company.

"Bill is one of the all time great CEOs in American business history," he wrote.